
House vacation rentals in Winter Park
Find and book unique houses on Airbnb
Top-rated house rentals in Winter Park
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Park house rentals
House rentals with a pool

Private pool home near Downtown

The Shire -Private Pool & Hot Tub, Close to parks!

Gated community XL pool Home 2500sq/f

Stylish Villa Private Pool-SPA Near Parks Disney!

Country Pool home on 2 acres-30 minutes to Disney

Pool House in Kissimmee

4BR-2KingMasters-SpaHeat-Private Pool-Remodeled

Family Home Gated 10 Beds Pool Disney 7 miles.
House rentals with free parking

Universal private room!

6Bdrm home near Disney/Free Pool Heat/Waterpark

Modern Legends, Near Disney, kings bed ste

Quiet Cozy Haven

Charming Central Orlando Home w Private Yard Porch

Pretty - Comfy (near Universal)

The Calm Green One - Downtown

A Rare Jewel in the heart of Winter park. Can walk
Weekly house rentals

Pet-Friendly Bungalow Near Downtown Orlando

969T-Single Storey House 20 min from Disney 4 bed

9001-WW 5 Bedroom ALL Suites Pool Home

5BD Windsor Westside Private Pool (WW 9025)

3/2 Family Home, climatized Pool and Sunset Views

BRAND NEW 10Bedrms/Sleeps22 At Windsor Island

Spacious 4 bedroom single story home

5 ⭐️Gorgeous*Gated*15 Min.Disney*Wi-Fi*GameRoom
Quick stats about house rentals in Winter Park
Total rentals
170 properties
Total number of reviews
5.1K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Destinations to explore
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- Disney's Animal Kingdom Theme Park
- Disney Springs
- SeaWorld Orlando
- Cocoa Beach Pier
- ESPN Wide World of Sports
- Daytona International Speedway
- Universal Orlando Resort
- Reunion West
- Amway Center
- Kissimmee Lakefront Park
- ChampionsGate Golf Club
- Epcot
- Disney's Hollywood Studios
- Universal's Islands of Adventure
- Magic Kingdom Park
- Blue Spring State Park
- Aquatica
- ICON Park
- Things to do Winter Park
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- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes